12 Emails You Shouldn’t Send Your Boss or Colleagues

Savvy email users know that there are numerous types of emails that you should never open, particularly if you’re worried about email scams and don’t quite trust your spam filter to catch everything for you. But, did you know that there are plenty of emails that you should never send, as well? From messages that compromise your security to those that simply show bad etiquette, the email types ahead are ones that you should never hit “send” on.

1. An email written to avoid a difficult conversation

businessman presenting at a meeting

It’s important to discuss important issues face-to-face rather than over email | iStock.com

Whether you’re dodging a discussion with your boss or your mom, you should never write an email simply to avoid or put off a difficult conversation. Bringing up a sensitive topic, trying to resolve a conflict, breaking bad news, or negotiating for a raise or a promotion are all conversations that are better completed in person. That way, you’ll be able to see how the person reacts and steer the conversation accordingly, rather than sending an email and waiting anxiously for a reply.

2. An email reprimanding someone

Man researching on his desktop computer

You should avoid reprimanding someone over email | iStock.com

Whether it’s the intern you supervise at work or the contractor who keeps ignoring your instructions, it’s never a good idea to reprimand someone in an email. The most effective conflict resolution is typically done in person. And, if you need to tell someone that they’ve done something wrong, communication will usually be clearer (and the resolution will be reached more quickly) if you have that discussion face-to-face.

3. An email asking for a favor from someone you don’t know

Business people working in their office

Reaching out via email just for a favor is never a good idea | iStock.com

Most industries are relatively small worlds, but if you need a favor from someone whom you don’t actually know, email may not be the best way to get in touch. It might be more ideal to take someone to lunch or coffee to formally introduce yourself and have your discussion. If you aren’t in the same city or don’t foresee your paths crossing, get a mutual acquaintance to send an email that introduces you first. Penelope Trunk, a notable businesswoman and author, reports that nobody should be sending emails that are the equivalent of cold calls, since they are rarely worth the time that you put into them.

4. An email inviting someone to lunch instead of one asking them for information

Business colleagues working together

Be direct in your emails and request the information you’re looking for | iStock.com

Trunk also advises against sending an email inviting somebody to lunch when they could provide the information you need — whether that’s advice, connections, or support — via email instead. As Trunk points out, most people who have a lot to give don’t have a whole lot of time to give it, and lunch takes more time to conduct compared to an email conversation. When in doubt, send an email requesting the information you need. Trunk advises, “The rules for how much time you can ask of someone seem complicated. But the bottom line is, don’t invite someone to lunch unless you plan to give them money.”

5. An automated email saying that you’ll be gone for a day or two

Man pointing at a woman's computer screen at work

Automated email responses are useful, but know when and where to use them | iStock.com

Automated email responses that explain that someone will be out of the office for a week or longer are useful, since they tell the people who are contacting you that they may want to get in touch with someone else if the matter at hand is urgent. But, don’t turn on an automated response if you’re only going to be out of the office for a day or two. Automated responses are annoying, and if you won’t be gone long enough for your reply to be significantly delayed, it isn’t worth drawing attention to your absence.

6. An email that’s forwarded without careful thought

Man slumped over his desk at work

It can be costly to forward an email to the wrong recipient accidentally, so be mindful of this | iStock.com

It may seem like a good idea to forward a message, since that can be the fastest way to get someone the information they need without composing a brand new message and starting a new thread. But, if you choose to forward a message, you should always look carefully through the entire thread. It’s far too easy to accidentally send someone a thread that has either more information than they need or a conversation that the recipient was never meant to see. Read through the entire thread to make sure that there isn’t any information that could offend someone, and think about whether it’s a better idea to just create a new email instead.

7. A copy of every email you send

Man holding smartphone and smiling

Look more confident in your emails by not copying your boss and co-workers on every email you send | iStock.com

Whether you’re copying your boss on every email that you send to a client or copying your co-worker on each message that you send regarding a shared project, indiscriminately copying somebody on tons of emails is a great way to annoy them. It’s also a sure way to give them the impression that you aren’t confident about the decisions you’re making, or are relying on them to ensure that you aren’t making any mistakes. Either way, that’s not a good way to enhance your reputation around the office. A better policy is just to handle your emails yourself and update co-workers and supervisors as necessary.

8. A message that poses an open-ended question to a large group of people

Man typing on his laptop at his desk

Be concise with your emails, and don’t send open-ended emails to large groups | iStock.com

If you’re trying to keep your electronic communications efficient and time-effective, then one of the worst emails you can send is the kind of message that poses an open-ended question to a large group of people. Asking an open-ended question about an important subject, and asking a large group of people for their feedback, is the perfect way to start a thread that stretches on and on and requires people’s attention multiple times throughout the work day. While it might seem like an email would be a more efficient way to get a consensus than a meeting, the opposite is often true, and you may be better off discussing the details in person rather than trying to parse out everyone’s responses from your computer screen.

9. An email expressing a concern that you aren’t ready to discuss

Team of co-workers having a business meeting

Wait to discuss larger concerns over email until after the weekend is over | iStock.com

While you might think that it’ll save time to let people know which issues you plan to tackle the next work week, you should never start the weekend by sending an email expressing a concern that you aren’t yet ready to discuss. It seems like a good idea to give someone a heads-up about what you want to discuss after the weekend, but if the concern is about someone’s performance or is their responsibility to resolve, then this becomes an unfair and inefficient way to communicate. If you express a concern, you should be ready to talk about it right away, rather than hoping just to pass it off for that person to think about all weekend.

10. An email without a clear subject line

Man holding his head at work

Always be clear with the title of your emails | iStock.com

We’ve all been there before: searching for an email that had a generic, vague subject line, but actually contained some important information. Many people waste significant amounts of time searching through an email for the information that they need, and knowing the info that the email contains is even harder if it isn’t labeled clearly. Your boss definitely doesn’t want you making it any easier for people to waste time, so always try to choose clear subject lines for the emails you send.

11. A message that isn’t work-related or isn’t necessary

Businessman looking at his laptop

Always send emails that are relevant when you’re at work | iStock.com

People get too many necessary emails already, so they really don’t need you emailing them cat videos. (That’s what Slack is for, obviously.) Many employers fire workers for sending emails that aren’t work-related, and plenty lose money each year thanks to employees having to spend their time dealing with unnecessary emails. You should always think twice about sending emails that are unnecessary or not related to your work, since it’s not just your productivity that can take a nosedive when you hit send.

12. Any email sent while you’re angry

Man sitting alone in an office

You may regret sending emails when you’re angry | iStock.com

Just as it’s best to have difficult conversations in person so that the discussion is likely to remain respectful on both ends, it’s also a good idea to avoid starting email threads when you’re angry. It’s easy to fire off an email when you’re mad about something, which may make you feel even more justified in using harsh language and curt syntax. But, if you’re really angry, it’s best to wait to hit send — or to delay writing it at all — until you’ve calmed down and can judge more clearly what needs to be said and what’s better to avoid writing.

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